Rule 1: Invest your money on a book on How to Flirt
by queensage
Summary: Sydney Sage: CEO of Millionaire MatchMakers Club. A Dating service attempting to match wealthy clients for others looking to date Sydrian FanFiction
1. Chapter 1

**A/N: Hey y'all, this is actually my first Sydrian story and would love honest critical reviews :) tell me what you think! I'm not sure if this will become a full on story but if most of you do love it, I shall continue. I guess I'm just testing it out.**

**Disclaimer Do not own of the characters. Rightful owner is Richelle Mead: Bloodlines **_but I so wish I did more specifically Adrian ;)_

_Rule #1: Invest your money on a book on "How to Flirt"_

10:00 pm. Sydney let out a yawn. Late nights at the office were a normal thing for her, it was usual for her to leave around this time from work while the rest of her co-workers clocked out at 5pm. Matching people with the right person was a hard job but she loved it. She started her very own dating service she personally designed attempting to match wealthy clients to other people looking for love. It started off as a small business but soon became an expanding one. Her success rate being the highest, many lonely ones tired of looking for love came to Sydney for help. The blonde had a name for herself, Sydney Sage, CEO of the Millionaire's Matchmakers Club. All of New York knew her title which is how she liked it.

All she wanted to do was go home and lay on her bed for the sleep she was yearning for. That would be the best way to wrap up the year, she thought. She stepped out her car and quickly headed to her condo. Late December nights were extremely cold, she cursed underneath her breath as she wrapped the small black blazer around her tiny frame. She took out her keys and opened the door to find her best friend Rose at the entrance in a dress putting on her last heel. The blonde giving her a once over and felt a pang of jealousy come over her. Rose's body was to die for; the long dark haired beauty was tall and curvy in all the right places.

"Where are you going so late?" Sydney asked closing the door behind her.

"There you are! I called you so many times but I guess my calls didn't get through." Rose sarcastically said. "Now hurry up and get dressed", she added while making her way to the bathroom.

Sydney gave her a dazed look. _The only thing that I'm getting ready for is bed, _she thought. She set her things down on the counter and followed Rose into the bathroom. "Where are you even going?" she asked again.

Rose stopped fixing her hair and looked up at Sydney. "Why are you still here, go change and put a sexy dress on, we have a party to attend."

"Party?" Sydney questioned. Maybe it was the sleep that was getting to her. She seriously did not understand what her best friend was talking about.

The dark beauty rolled her eyes slightly irritated that her friend was being a little slow. "New Year's Eve party, remember?"

_No, actually I did not remember_. She tried to retch her brain of a party she was supposed to attend but she came up with nothing. Rose rolled her eyes once again and said, "Sydney, just get dressed."

"But I don't want to." Sydney yawned. "I'm sleepy."

"You can sleep when we come back later, besides it's not like you have to go to work early tomorrow."

"Correction, I have a meeting with one of my clients early in the morning." Sydney tried to lie even though they both knew along with the world how horrible she was at keeping a straight face. She really was not in the mood to attend a party right now. All she wanted to do was topple on her bed.

"Go change, do not play with me Sydney. I'm your best friend."

"I don't want to go!" Sydney replied crossing her arms and taking on a stance of a two year old about to throw a tantrum. Crowded, social setting were not her thing. She could handle crowded meetings even conventions but parties, nope count her out of it.

Rose ignored her and finished applying her makeup.

Syndey already knew she lost the battle, there was no way getting through to her friend and sadly there was no way that she was going to be reunited with her bed anytime soon. She let out an exasperated sigh and lazily made her way into her room. She looked in her closet for something nice to wear. One of the reasons she hated parties was because she had to abandon her comfortable pair of dress suits. She was thinking about just going to go out in the pant suit she was already in, she was sure she would win the argument with Rose since she was forcing her to go to this god forsaken party she didn't want to in the first place but thought against it in the end. Her argument with Rose would take up a considerable amount of time which would delay her reuniting with her bed plus she had no energy left to put up with an argument. She settled for a black dress.

Rose came in to the room minutes later and took a look at Sydney. She gave her a dissatisfying look. "You're not going out with me looking like that."

"What? Why?" Sydney said looking down at the dress she slipped on. _There was nothing wrong with what I'm wearing, besides who am I trying to impress, _she thought to herself.

"We're not having New York's notorious matchmaker go out like that." Rose replied walking into the closet. After a few seconds, she emerged with a red dress in hand. "Here, wear this dress." She said tossing it to Sydney.

Sydney caught it quickly and looked at it. It was a pretty dress but also a revealing one. "I'm not wearing this." she quickly replied.

"Yes, you are."

"No, I'm not."

Her friend gave her a look in which rightfully Sydney returned back.

Rose let out a sigh. "Sydney, how do you expect to find a boyfriend looking like that?"

"Not this again!" Sydney rolled her eyes. Rose was once again trying to find her boyfriend. Hasn't ever occurred to her that maybe she didn't need one? Ever since Sydney matched her once single friend with a client of hers a few months ago, Rose has been dying to get Sydney a boyfriend as well. She knew her friend met no harm but she was too busy concerned with her client's love lives, she didn't have time to think about her own.

"Come on, Sydney. There's actually a guy I know that would be great for you!

Sydney rolled her eyes once again. Here we again, once this conversation started, it seemed it would never end. _'Why don't you worry about your own love life?'_

"You know, ever since you set me up with Dimitri, I've never been so happy." Rose continued, "Maybe you wouldn't come back so tired and cranky if you had one."

Dimitri Belikov, a client of hers who not too long ago stepped in to her office looking for a "the love of his life."

After a few minutes of Rose ranting the pros of having a boyfriend, Sydney did the only thing that could shut her up. She went to the bathroom taking the red dress with her.

"You look beautiful! I still don't understand why the guy's haven't fallen for you. Those legs are just so long and sexy and that dress accentuates your waist perfectly." Rose answered once Syndey emerged from the bathroom. She felt uncomfortable as Rose looked her over one more time and smiled to herself like a proud mother. Sydney hated compliments more than anything, it made her feel uneasy plus she wasn't really the biggest fan of her body. She tried pulling her dress down which wasn't doing much, it came up to her mid thigh.

"Stop that" Rose said slapping Sydney playfully on the arm.

"I'm showing too much skin" Sydney scowled.

"Duh, that's the point." Rose looked over once more and smiled from ear to ear, "we need to get you shoes!"

She watched as her friend ran back with a pair of black heels. "Here, wear these."

Sydney took it from her and put them on. "Okay, I think I'm ready. Let's go please, the faster we go, the faster I can get home and go to bed."

Rose nodded and grabbed her bag and keys. They both headed to the door when Rose suddenly stopped bringing them to a halt. "What's wrong?" she asked confused.

Rose turned around and reached for the back of Sydney's head until she found an elastic band. She pulled it off, causing Sydney's hair to fall in place. "There. I just had to do that. Your blonde locks do not deserve to put in a ponytail." She said throwing the elastic band away.

Sydney stifled a laugh and rolled her eyes. Her best friend was something else.

Drinks in hand, crowded spaces, loud music bodies shuffling from place to place, this was not a comfortable setting for Sydney. She wanted to leave the second they both stepped inside. She was extremely tired, she felt like her body was going to give out any moment. She scanned the area till she saw something that caught her eye. "Can we get a drink first?" she asked Rose, pulling her in the direction of the bar. If she had to be here, she was going to make use of the bar, maybe a few drinks in her system would help her relax a bit.

"Well, hello there, beautiful ladies, how may_ I_ be of service?" A man in his late twenties behind the bar greeted them once they arrived. He was a tall handsome man with emerald green eyes and dark messy hair. She looked him over twice and thought he'd be quite cute if it wasn't for that god-awful greeting.

"Just drinks, nothing more please." Sydney quickly replied.

The bartender crookedly smiled and responded, "Just drinks?"

_Was he serious? She mentally noted to herself to hand him her card, her services included "How to Flirt 101" sessions._

"Yes, _drinks_ will be all." She heavily put emphasis on drinks, which earned her a smirk.

"Where do you think Dimitri is?" Rose asked completely oblivious of what just happened.

Sydney shrugged and replied, "I'm not his mother, Rose." She didn't mean to sound snarky but it ended up coming out that way.

"Thanks." Before Sydney could apologize, Rose pulled out her cellphone and answered the other end. Her mood drastically changed, equivalent to a person on cloud nine. Dimitri was clearly on the other end of the line.

The bartender came by and set the drinks down in front of Sydney. "There you are, two cold refreshing alcoholic beverages made by yours truly."

She responded with a curt nod and thank you. She took a long sip, practically inhaling the drink. Satisfied she set it down, alcohol already taking it's course. She always was a lightweight when it came to drinking, something her friends teased her about relentlessly.

"From a guy who knows a lot about drinks, you should slow down."

The voice came from the man behind the counter. "Not saying you can't handle your liquor but I've never seen someone down a drink so fast."

"I'm trying to get through the night." She responded. "And don't tell me how to handle my drinks." She added.

He let out a deep laugh and held out his hands in defense, "Can't scold a guy for trying to look out for his customers."

Sydney gave him a hard stare but it slowly softened. Maybe she was being too harsh? She chased away her best friend or well technically that was Dimitri's doing and now she was practically about to eat the head off of a man she barely knew? Hell, it wasn't his fault she was here. Would it kill her to let loose and not be so guarded?

"Sorry, it's been a long night. I don't exactly want to be here." She let out a yawn and stretched hoping it would it wake her up a bit.

The man looked at her and smiled once again. He was about to say something before he was interrupted by a dude adjacent from the bar. "Drinks Adrian!"

"Sure thing" the bartender replied. He gave Sydney what she assumed was a 'I'll be right back look' and left to go tend to the party goers.

She took her phone out hoping to find a text or missed call from her assistant Jill to at least keep her busy but she had no luck. Of course Jill would be out with friends, having a great time on New Years Eve. Was she the only one on planet earth that wanted to enjoy New Years Eve in the comfort of her bed? She yawned again, the thought of sleeping taking over her body. She opened up her email and decided to look through her never-ending mailbox to keep her busy.

"Are you seriously looking through emails right now?" a voice behind her said, she turned around to find Rose and Dimitri closely wrapped around each other.

"What's wrong with that?" she replied back.

"Sydney, get up!"

"I rather not, I'm quite comfortable."

Rose rolled her eyes showing defeat and Sydney smugly smiled to herself. "Fine. Stay sedentary until your ass falls off. Anyway, Dimitri was telling me about some guy at work who would be perfect for you" She gleamed, eyes widening as she told Sydney. "We could do double dates!" She squealed.

Sydney shook her head, Here we go again. Was it too much to ask for at least one night off from Rose's conniving plans to set her up? She knew she met know harm but it was getting tiring.

"He's a really good guy Sydney" Dimitri spoke up, "Give him a chance."

"Not you too." Sydney whined in response. Rose was enough but now her boyfriend, Sydney could handle one but two people nagging her about her love life was too much.

"You have matched me up with someone I truly love; it's the least I can do setting you up with a friend of mine."

Sydney glanced at Rose who was smiling from ear to ear. She didn't know if it was the fact that Dimitri said he loved her or the mere fact that she was actually getting help trying to find her a boyfriend. She couldn't believe these two, she desperately wanted to escape this conversation. "I don't need one, you guys, really." she argued.

"Yes, you do." Rose argued back.

"Everyone needs a boyfriend, even a love guru, Sydney" Dimtri said in a matter to faculty tone.

Sydney couldn't help but feel annoyed with these two trying to fix her love life. '_Why don't they just worry about themselves?'_she asked herself. She was really regretting setting them up in the first place.

The New Years count down finally started which apparently shut up Rose and Dimitri. Everyone turned their eyes up to the ceiling while counting down to one, apparently anticipating something. Once the countdown reached one, the ceiling opened up to reveal a huge ball with the new year written on it, along came down strings of confetti. The whole crowd of partygoers hollered, while majority of them grabbed each other to kiss. Dimitri wrapped his arms around Rose's small waist, bring his mouth down to hers.

"Happy New Year's." The voice behind her said, she turned to see Adrian wiping the counters. "Do I get a New Year's kiss?" he asked half smiling, half smirking.

She hopped off her stool excitedly, not even Adrian's awful lines could ruin her good mood due to getting to leave the party finally and be reunited with her bed. "Nope...but you do get this." She grabbed her wallet and pulled out her card. "Come by sometime, that is if you'd like to perfect your flirting." Sydney genuinely laughed to herself by the amused look he returned leaving him speechless for once. "Happy New Years" she finally said before leaving to go grab Rose.

**a/n: sorry if this didn't have enough Sydrian moments but the next chap sure well! Stay tuned and leave a review!**


	2. Chapter 2

**A/N: Hi you all, thank you for those who have reviewed and followed/faved. You are truly the best. I really wasn't thinking of continuing this story but I think I will! :) **

_Rule #2: Under any circumstances you will not be able to start any sort of __**relationship **__**other than business**__ with the CEO of "Matchmaker's Club" _

"Jill!" Sydney screamed from her office while typing a rapid email.

The tall beauty came running in at the speed of light, "Yes, Miss Sage".

"I need you to make copies of these files to my left and then input them in the database." she replied without turning away from her computer screen. "Tell Eddie to start matching up possible clients and have him check back with me." She then sent her assistant on her way and continued typing.

It was a hectic morning and it was only a quarter past ten. She got up and stretched herself out. Mentally cursing Rose for the reason being her body was still recovering from last night's party. It's not like she did much anyway other than sit on a stool majority of the night but her body felt like she hadn't slept in ages and although she did agree to attend the New Years Eve party, it satisfied her to blame someone else for it.

She stepped out her office announced loud and clear, "I'm going for a coffee run, you know where to reach me if any problems do arise while I'm gone." With a variety of head nods shaking in her direction from her employees she took that as a sign to leave. She knew she could've asked her assistant to do it but she felt like she was in need of fresh air anyway.

She stepped outside and was met with tons people walking in every direction. She loved New York, everyone looked as if they were on a mission to achieve something. Life seemed to always be moving, never slowing down here. There was no relaxing which she loved, it drove her to be motivated in a way and inspired her work ethics. Coming to New York was the best decision she ever made along with her actually starting a business. She was told she wouldn't succeed by her father when she made the choice to do this as a career but he couldn't be more wrong.

"Thanks." She said to an individual holding the door open for her. She stepped inside the cafe, the sweet aroma of coffee beans taking over her olfactory senses. She was a huge coffee lover, if she could live with one thing only, it would most definitely be a coffee machine and some coffee beans; she needed nothing else in life. After finishing up her order, which was quite huge considering she ordered for all her employees, she didn't have to but she was feeling extra nice today. The mood was good.

She heard her name being called by a cafe employee indicating that her order was ready to be picked up. She thanked them for their service, grabbing the two cup holders that held four cups of coffee each and headed for the door. Juggling eight cups of coffee wasn't the easiest task she soon figured out once she reached the door, opening it was the biggest obstacle she faced. She decided to use her elbow to push the door open but her elbow never ended up reaching it. The door ended up swinging open as a man walked in. Before Sydney could move out of the way, the man didn't register her presences quickly enough and bumped in to her. The result was horrible, what seemed like a horrific slow motion picture in just a matter of seconds played out in front of her. The cup holders escaped from Sydney's grasp and went flying in the air in every direction and hit the floor. She shrieked in shock as if it was a murder scene that she witnessed which to her it kind of was, good coffee on the floor ruined.

"I am really sorry about that….I didn't see you."

She tore her eyes away from her precious coffee to stare at the culprit responsible. "You!" She instantly recognized the green and dark hair. "Why- how -my coffee-" she stumbled out. Her mind still hadn't registered from the terrible fate of her coffee. She frowned at him.

"Hey, aren't you the girl from-" He never got to finish his sentence when Sydney interrupted him. "Why did you do that?"

"It was an accident! You don't actually think I'd do this on purpose?" He scoffed completely baffled by her accusations. "What am I, New York's villain causing harm to citizens on _purpose_?"

"Yes!" Sydney answered a little too quickly. She looked at her coffee again. Two employees at the cafe had come to clean it up. One of them looked up at her and asked, "Would you like another order Ma'am?"

She nodded and glanced at Adrian behind her, "He's paying for it."

"Me? You were technically in my way! And who the hell orders twenty cups of coffee anyway?"

"I do." she answered crossing her arms across her chest. "Are you not aware of your surroundings to begin with? You do not just open a door so hastily without being sure there isn't someone behind it doing the same. It's common courtesy, it is called manners, it's-"

"Fine, fine fine." He quickly responded shutting her up. "Giving someone a lecture in a condescending tone won't help you get your point across. I'll pay for the stupid coffee." He left her speechless as he walked on over to the cash register.

Sydney closed her once open mouth at his remark. Did she come across as rude, she wasn't trying to she was just getting a point across. What was he mad for anyway, she was the one who lost the lives of her coffee. She had a right to be mad!

"Here." Adrian said approaching with a fresh batch of coffee. She expected him to give her both cup holders but he told her he'd hold on to the other one and help her carry it to her destination._ Good, _Sydney thought. The least he could do for making her feel like shit for about half a second.

"So….", he started, breaking the awkward silence the surrounded them as they walked the three minutes it took to get to her office, "What's all this for, is your boss making you do a coffee run or something?"

They reached the end of the crosswalk; she pressed the button on the pole to activate the flashing signal to walk. "Nope, I am my own boss." she answered him. She couldn't quite see his face since she was too busy looking at the light till a walking symbol appeared on it but she was certain it was a look of surprise. It was the usual look she got once she told people she ran a company, and a greater look of surprise when she told them she was only twenty-three. It was quite quiet again, the only sound coming from the signal to cross and hurried foot steps from people crossing as well. They reached the building and walked inside but came to halt once Adrian saw a sign hanging on the wall with Sydney on it. _"Matchmaking Center, located on Floor 3! Your potential loved on is waiting, come give us a visit!" _

Her face turned a shade of red equivalent to a tomato. She was meaning to take down the sign just for the cheesy-ness of the slogan but never came around to it, plus the fact she was on it holding a red plush heart made it worse.

"So…..you run a dating service?" He asked, a look forming on his face as if putting the pieces together. He then fetched something out of his pocket. "Now it all makes sense!"

Sydney glanced at what he held, she noticed it was a card, her card to be precise, the one she forgot she gave him last night.

"You know….", he continued, "I thought it was weird, a really pretty girl handing me a business card, something about teaching me to flirt, which I must say left me at a loss of words. I thought it was a clever pick up line." He glanced back at the card again. "but this is more interesting, Sydney Sage." His name rolled off his tongue in amusement enjoying the whole situation

"The coffee's getting cold." Sydney stated and headed to the elevator completely ignoring what he just now concluded. To be honest she really didn't know what to say to him and ignoring him was her next best choice. He followed right after not letting go of the conversation, "Are you trying to set me up?" He questioned a smirk playing off his lips.

"Of course not." she replied and stepped inside the elevator pressing "3". "From what I have observed last night, you need a bit work on how you come across to women more specifically how you flirt. It's one of the first things we tackle, it may be the reason for most as to why they have trouble finding a loved one."

He belted out a laugh, a laugh that never seemed to end. From the way he was uncontrollably laughing it's as if Sydney told him the funniest joke in the world which Sydney found extremely disrespectful. He was clearly finding this all too amusing, was she a comedian now? They had finally reached the floor, Sydney stepped out instantly yelling for Jill. The tall beauty appeared at the speed of light. Sydney grabbed one coffee cup and handed the rest of the remaining coffee in the cup holder to her assistant. She turned to Adrian who was still wearing that god damn smirk on his face, she wanted to slap him but she forced a smile instead. "You've done enough, thank you. You can hand over the rest of the coffee to my assistant and see your way out." Satisfied, she turned on her heels and headed for her office.

A satisfied "mmmmm" escaped her lips as she sipped her coffee in pleasure. She never knew how people survived without the enticing smell and amazing taste of coffee. She tried to swear off the caffeinated drink once but failed tremendously only being able to live without for about three hours. Coffee was definitely her drug.

"Miss Sage," a voice came from the door to her office.

"Come in." She replied.

In came Jill with an uneasy look. "The man that helped you deliver coffee is still here and he'd like to speak with-" Jill never finished her sentence when the devil himself walked in. "It's Adrian" he corrected her.

Sydney's face took on a look annoyance. She was beginning to think he was created by god just for the purpose of irritating her. "Is there something else you need?"

Her assistant glanced back and forth from Sydney to Adrian feeling the uncomfortable tension in the room. "I-I can leave Miss Sage."

"No, stay.", Sydney commanded bringing Jill to stop at mid-walk to the door. "Adrian will be leaving pretty soon anyway. I'd like you to show him out." Sydney ordered, then turned her attention to the dark-haired male and repeated her question.

"I'd like to join." He answered confidently.

Sydney stared at him intently for about a long minute in order to see if he was bluffing. She didn't detect sarcasm in his voice either, he serious. Quite frankly she did not want to see him again and adding him to her Matchmakers Club would mean constant appointments scheduled with her. She was about to refuse when she noticed her assistant still in the room. Replying with a no would start a train of questions she wasn't willing to deal with especially questions concerning Adrian.

She pursed her lips in dissatisfaction. "Okay. Jill, add the mister here to our client list." Sydney shooed them away, she wanted him out of her hair already, she would find away to deal with him next week. She was about to return to the tasks on her computer that she left earlier but was interrupted from doing so.

"Oh, no need Sage," he walked closer to the desk but stopped once Sydney scowled, "You're in my office therefore it is Miss Sage."

"Miss Sage, it is." He was entertained, Sydney could tell. His demeanor, facial expression, the damn smirk playing on his lips, he was enjoying this making Sydney more annoyed as a result than she already was. She couldn't let him know that though, it was definitely what fueled him. She plastered a small smile on her face, "Continue."

"I want to date the CEO of this establishment."

Sydney's face turned the same color red from earlier, this time her face heating up along with it. She composed herself and ordered Jill to leave. Once they were both alone with the devil himself she responded, "You can't do that."

"Why not?" He smiled enjoying the reaction he got.

"B-because…." She didn't have an answer for him, she was never asked for this request by any of her clients. For the first time ever, perfect, organized Sydney Sage did not have an answer already prepared before hand. "Because you just can't", she lamely said.

**A/N: Review, follow, fav and all that other wonderful stuff. I really enjoyed writing this chapter probably for the many Sydrian interaction. There will be more to come for sure in the next update **


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